Acetic Acid → 5-methoxynaphthalene-1-carbaldehyde

HRID 2060862Notes

Reaction equation

HRID 2060862 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]#N.CC(C[AlH]CC(C)C)C.C(O)(=[O:26])C.O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[CH:13]=[O:26]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14487Diisobutylaluminum hydrideHCID 13491715HCID 13491715, compound

Product 1

HCID 115138875-methoxynaphthalene-1-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 5-methoxynaphthalene-1-carbonitrile (Preparation 11) (1.1 g, 6.00 mmol) in DCM (40 mL) at −78° C. under nitrogen was added DIBAL (1.0M in toluene, 18 mL) dropwise over 10 minutes. The reaction mixture was stirred at −78° C. for 1 h, warmed to rt for 1 h and then cooled to 0° C. Acetic acid (1 mL) followed by water (1 mL) were added. The mixture was partitioned between EtOAc (100 mL) and water (100 mL), the organic phase was separated and dried (MgSO4). Solvent was removed in vacuo and the residue purified by column chromatography (EtOAc:isohexane 2:8) to give the title compound: RT=3.54 min; m/z (ES+)=187.0 [M+H]+.

Workup

  1. temperaturewarmed to rt for 1 h
  2. temperaturecooled to 0° C
  3. additionwere added
  4. customThe mixture was partitioned between EtOAc (100 mL) and water (100 mL)
  5. customthe organic phase was separated
  6. dry with materialdried (MgSO4)
  7. customSolvent was removed in vacuo
  8. customthe residue purified by column chromatography (EtOAc:isohexane 2:8)

Sources & evidence

ORD record
ord-c290f49081e24746842876c732e768dd
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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